Salicylic Acid → (R)-methyl 2-(2-hydroxybenzamido)-3-mercaptopropanoate

Participants

Reaction Steps

Separately, salicylic acid (152 mg, 1.10 mmol) was taken up in CH3CN (10 mL) along with L-cysteine methyl ester hydrochloride (189 mg, 1.10 mmol), EDCI (350 mg) and N-methylmorpholine (120 μL). The reaction mixture was stirred at room temperature for 3 h. It was then diluted with EtOAc. The organic layer was washed with saturated aqueous NaHCO3 and brine. The organic layer was dried over Na2SO4 and concentrated under reduced pressure to afford crude (R)-methyl 2-(2-hydroxybenzamido)-3-mercaptopropanoate. This material was then taken up in CH3CN (3 mL) along with (4Z,7Z,10Z,13Z,16Z,19Z)—N-(2-(2,5-dioxo-2H-pyrrol-1(5H)-yl)ethyl)docosa-4,7,10,13,16,19-hexaenamide (315 mg, 0.7 mmol) and stirred at room temperature for 30 minutes. The reaction mixture was then concentrated under reduced pressure. Purification by silica gel chromatography (CH2Cl2) afforded (R)-methyl 3-(1-(2-(4Z,7Z,10Z,13Z,16Z,19Z)-docosa-4,7,10,13,16,19-hexaenamidoethyl)-2,5-dioxopyrrolidin-3-ylthio)-2-(2-hydroxybenzamido)propanoate (140 mg). Mass calculated for C39H51N3O7S: 705.34; found: [M+H]+=706.

Provenance & Evidence